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16 Things Women Pretend to Like on First Dates (But Actually Hate Them)

Updated on November 3, 2025 by TMM Staff ยท Dating & Confidence

A man in a suit with a drink in hand has his arm around a woman in a light-colored dress.
ยฉcottonbro studio/Pexels.com

First dates are funny because half the time, everyoneโ€™s faking something. The smiles, the nods, the โ€œoh wow, thatโ€™s so interestingโ€ replies. Women, especially, have mastered the art of pretending to be charmed while secretly wondering how fast they can leave without looking rude.

Sometimes, women pretend to like something a guy says just because they want to give a guy a fair shot. Maybe heโ€™s nervous, maybe itโ€™s the lighting, maybe heโ€™s not usually this much. But by the time the appetizer hits the table, they already know if this is going anywhere.

Hereโ€™s the truth you wonโ€™t find in any dating guide. The stuff sheโ€™s enduring while saying, โ€œNo, really, itโ€™s fine.โ€

Table of Contents

Toggle
  • 1. Long Stories About Gym Routines
  • 2. โ€œFunnyโ€ Stories That End With โ€œYou Had to Be Thereโ€
  • 3. Fancy Restaurants Where You Canโ€™t Pronounce Anything
  • 4. Over-Explaining โ€œMan Stuffโ€
  • 5. Overly Aggressive Flirting
  • 6. Endless Talk About Exes
  • 7. Trying Too Hard to Impress the Waitstaff
  • 8. Overdoing the โ€œGentlemanโ€ Act
  • 9. Talking About Money or โ€œSuccessโ€
  • 10. Ordering for Her
  • 11. Talking About How โ€œChillโ€ You Are
  • 12. Making Everything a Debate
  • 13. Excessive Phone Checking
  • 14. Fake Deep Conversations
  • 15. Over-Complimenting Her Looks
  • 16. Acting Like a Walking Dating App Profile

1. Long Stories About Gym Routines

A man working out on a chest press machine in a gym.
ยฉAlesia Kozik/Pexels.com

We get it. You love to work out. Sheโ€™s nodding, pretending to care, but her soul left the table three flex stories ago.

Talk about the gym once, but make it your personality? No. Unless your dateโ€™s wearing a โ€œBorn to Squatโ€ hoodie, save it for your workout buddies.

2. โ€œFunnyโ€ Stories That End With โ€œYou Had to Be Thereโ€

A man and woman laughing together while sitting close indoors.
ยฉcottonbro studio/Pexels.com

If she has to fake-laugh, sheโ€™s dying a little inside. When a guy starts a story with โ€œYouโ€™ll love this,โ€ and it ends with โ€œGuess you had to be there,โ€ sheโ€™s silently praying for the check.

And you know whatโ€™s worse? When he laughs so hard at his own story, he snorts. Sheโ€™ll giggle to be polite, but her inner voice is already packing its purse. If youโ€™re telling a story, make it about something she can join in on.

3. Fancy Restaurants Where You Canโ€™t Pronounce Anything

A person reading a restaurant menu at a table.
ยฉcottonbro studio/Pexels.com

At first, sheโ€™ll act impressed. But after ten minutes of pretending she knows what โ€œfoie gras espumaโ€ means, sheโ€™s over it.

A good date doesnโ€™t need imported truffle dust. It needs good food, real laughs, and a place where she doesnโ€™t have to whisper her order like sheโ€™s summoning a demon. Sheโ€™d rather split tacos and laugh too loud than sit somewhere so fancy sheโ€™s scared to sneeze.

4. Over-Explaining โ€œMan Stuffโ€

A man and woman sitting at a small table with two glasses of wine.
ยฉcottonbro studio/Pexels.com

You know that tone? The one where a guy explains whiskey, poker, or car engines like heโ€™s tutoring a child? She hates that.

Sheโ€™s not nodding because sheโ€™s impressed. Sheโ€™s nodding to avoid saying, โ€œYou think Iโ€™ve never heard of horsepower before?โ€ The real flex is talking to her about stuff that she finds interesting.

5. Overly Aggressive Flirting

A man kissing a womanโ€™s hand while she smiles outdoors.
ยฉGustavo Fring/Pexels.com

A little charm goes a long way, but leaning across the table like youโ€™re in a music video? Sheโ€™s not swooning. Sheโ€™s planning her exit route.

Compliment her once and let it breathe. No one enjoys dodging a verbal tongue twister of pickup lines. And if youโ€™re staring too long, congratulations, youโ€™ve crossed from flirty to โ€œthis is getting weirdโ€ territory.

6. Endless Talk About Exes

A woman smiling at a man while sitting at a table with two empty glasses.
ยฉiam luisao/Pexels.com

Everyoneโ€™s got history, but the first date isnโ€™t the place for a breakup documentary. She might nod politely, but inside sheโ€™s thinking, Why am I hearing about your emotional damage over appetizers?

Bringing up your ex every few sentences is like inviting a ghost to dinner. If she wanted a haunting, sheโ€™d watch Netflix.

7. Trying Too Hard to Impress the Waitstaff

A person pouring red wine into a glass at a table with others.
ยฉPavel Danilyuk/Pexels.com

Thereโ€™s confident, and then thereโ€™s treating the waiter like your stage audience. Watching someone turn the poor server into part of their show is cringe in real time.

She doesnโ€™t care if the waiter โ€œknows you.โ€ She cares if youโ€™re kind. Being polite beats being a showboat every single time. And if youโ€™re tipping like youโ€™re tossing coins in a fountain, sheโ€™ll notice that too, and not in a good way.

8. Overdoing the โ€œGentlemanโ€ Act

A woman in a black dress and a man in a tuxedo sitting closely together on a couch.
ยฉcottonbro studio/Pexels.com

Opening the door? Great. Yanking it open so fast she almost trips? Weird. Chivalryโ€™s cute until it starts feeling like a play rehearsal.

Pull her chair out, sure. But let the gesture feel natural, not like you practiced it in the mirror a thousand times.

9. Talking About Money or โ€œSuccessโ€

A man in a suit standing at a bar with drinks in front of him.
ยฉMART PRODUCTION/Pexels.com

Dropping hints about your income or car brand is the last thing a woman wants to hear on a first date. Sheโ€™s pretending to be impressed, but really, sheโ€™s tallying red flags.

If youโ€™re bragging about your โ€œmultiple revenue streams,โ€ sheโ€™s wondering how soon she can stream away from you. Ask her about what she loves, not how much you spent on your โ€œOmega Speedmasterโ€.

10. Ordering for Her

A woman smiling while holding a slice of avocado toast and looking at someone.
ยฉcottonbro studio/Pexels.com

Old-school charm? No. Please no. Even if she smiles and says โ€œThatโ€™s fine,โ€ sheโ€™s probably fuming inside.

She can speak for herself. Unless she literally said, โ€œPlease order for me,โ€ donโ€™t do it.Bonus cringe if you say, โ€œTrust me, youโ€™ll love this.โ€ Well, she wonโ€™t.

11. Talking About How โ€œChillโ€ You Are

A close-up of two people sitting and holding takeaway coffee cups.
ยฉJohn Diez/Pexels.com

Anyone who keeps saying theyโ€™re chill isnโ€™t. When a guy repeats, โ€œIโ€™m super easygoing,โ€ sheโ€™s already bracing for the meltdown later.

If youโ€™re actually a chill dude, sheโ€™ll feel it. If you have to sell it, youโ€™re probably not. The biggest irony? The โ€œchillโ€ guys are always the ones who panic when the date doesnโ€™t go their way.

12. Making Everything a Debate

A man and woman sitting by a campfire and talking outdoors.
ยฉPavel Danilyuk/Pexels.com

Some men treat dates like podcasts, interrupting, challenging, and turning casual chat into โ€œpoint-counterpoint.โ€ Sheโ€™ll smile through it, but inside sheโ€™s screaming, This isnโ€™t a panel discussion, dude.

You donโ€™t need to agree on everything, but turning her every sentence into a sparring match is the fastest way to guarantee there wonโ€™t be a second date. Debate your friends. Flirt with your date.

13. Excessive Phone Checking

A man sitting at a restaurant table using his phone with wine glasses nearby.
ยฉJep Gambardella/Pexels.com

Thereโ€™s no faster way to kill chemistry than constant screen-glancing. She might pretend itโ€™s fine, but she noticed every single time.

Put the phone down. Look her in the eye. The text can wait. And if it canโ€™t, she wonโ€™t either. Nothing screams โ€œyouโ€™re not importantโ€ louder than someone scrolling mid-sentence. Youโ€™re not that busy: Youโ€™re on a date, not running NASA.

14. Fake Deep Conversations

A man and woman sitting at a table having a serious conversation over a meal.
ยฉTima Miroshnichenko/Pexels.com

Asking, โ€œSoโ€ฆ whatโ€™s your purpose in life?โ€ before dessert is justโ€ฆ awkward. Sheโ€™s pretending to reflect, but really sheโ€™s thinking, โ€œSir, I met you an hour ago.โ€

Talk about your worst vacation, your weirdest job, the time you ruined Thanksgiving. Thatโ€™s where the real bond forms. Keep the โ€œmeaning of lifeโ€ talk for when she actually likes you.

15. Over-Complimenting Her Looks

A man and woman sitting in a cafรฉ having a conversation over coffee.
ยฉPavel Danilyuk/Pexels.com

Compliments are great, until they start feeling like a script. โ€œYouโ€™re gorgeous. Stunning. Unreal. Flawless.โ€ It goes from flattering to weird fast.

One sincere compliment beats a dozen rehearsed ones. Tell her what stood out. Her laugh, her sarcasm, the way she talks about something she loves. Thatโ€™s how you make her feel seen. Otherwise, youโ€™re just another guy reading from the same tired playbook.

16. Acting Like a Walking Dating App Profile

ยฉWilliam Fortunato/Pexels.com

Some guys treat first dates like theyโ€™re reading their own bio out loud. โ€œIโ€™m really into hiking, I love dogs, Iโ€™m super spontaneous.โ€

Look, she wants the real thing. Talk like an actual person. Tell her about the worst camping trip youโ€™ve ever had, or the time your dog stole a whole rotisserie chicken. Give her a story that feels alive, not a resume that sounds recycled.

Dating & Confidence

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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